Our first times hardly go as planned. We fumble, stutter, mumble and end up settling for less than we're worth. If you happen to have a movie-moment first time, let me know, but mine was far from it. I barely recall that night, only seven years ago, but I do remember one thing--Donnie Darko.

I know, right? Random thing to remember, but that's what the guy put on to play on his TV to drown out my loudness, something we'd figured out already from the heavy petting we did in his '76 Mustang. You know, the awesome ones that had the bench front seats? Yeah, that thing was amazing. I love cars with bench seats; reminds me of that great time, the summer before I went off to college.

I was still seventeen, turning eighteen the first day or so into college, but I knew for absolute certain that I wanted my first time having sex to be taken care of before spreading my wings at band camp & college in less than a month. The guy, or boy I met and decided to share this special deflowering moment with was slightly older, maybe twenty or twenty-one, and fully alright with my underage-ness (ten days 'til my eighteenth and I promised him I was fully willing).

He was a co-worker's older brother, still living at home with her and their parents. We had started hanging out a month or so prior to that fateful August evening, after his sister had cancelled on my plans with her. At first he was just that older guy I looked up to, curious about life past my mediocre high school existence and enamored by his seemingly worldly charm. Back then I was still an innocent, naive young woman, who knew that she loved sex but wasn't quite sure how to test the waters. Brian helped me enter the new world of adult life and sexual intercourse.

We would walk hand-in-hand through his house to his back bedroom, fifteen feet of rooms and hallways to muffle the sounds of what actually happened back there. He had a TV and an Xbox in his room, well-equipped by my standards, and so we hung out back there at first under the pretence of gaming and nerding out. Like I said, "at first."

Over a couple weeks, we migrated to cuddling on his bed watching a movie, hitting first, then second base. After the movie ended he'd drive me home and we'd make out a block down from my parent's house. As strict Catholic parents go, the knowledge that your straight-A, high GPA high school-graduate, college-ready daughter was seeing an "older man" never sat well with them. So I let them think Brian & I were just friends.

He never pressured me and that much I appreciated now, but even then I knew I loved being the wanton sex fiend back then. We eventually worked up to the night in question, the taking of my cherry.

Brian knew that taking my virginity would be painful for me and bloody too, so we worked together to make that moment more enjoyable. I used a hairbrush handle on the nights we couldn't meet up and hang out, and every other time he would diddle my cute clitoris and finger me hard, never deterred by the little streaks of blood that happened almost every time. We also figured out that I really enjoyed working him up with my mouth and hands, like I still do today. If I could talk to Brian for five minutes today, I'd definitely have to thank him for a couple specific kinks in my sexuality--love of giving blowjobs, in particular.

But I digress, back to that lovely August night. It would be my last time seeing Brian and hanging out with him behind closed bedroom doors, and we knew that tonight was the night. We started watching Donnie Darko to relax and ease into the moment. Ten minutes in and Brian had his hands under my shirt, working the clasp of my bra, while my hands were playing with the hardness under his shorts.

After reaching in and fishing out his dick, (a monster to me then but now it would be only average) six inches at most and delightfully thick, Brian placed his hands on the back of my head and firmly lowered my mouth to envelop his growing member. Let it be noted, that's another kink of mine.

At this time, I didn't much care for what was on the screen, only for the hard throbbing piece of meat between my lips. I wasn't a pro sucker but with Brian's helpful tips I was learning each time, and this attempt made him moan and pant with need more than before. I grinned big and kept engulfing every inch just to witness his reaction. Wasn't long before it became too much and he pulled me up off his cock, strings of spit and precum dangling from my lips to the engorged head.

Whimpering at being detached from my favorite appendage, I moaned in protest but then in arousal as he pushed me down onto his bed and worked my skimpy shorts off. Brian was never one to reciprocate oral sex, but tonight must've been special enough to me that he decided to lick my clit and suck my sweet juices right out of me. Might've been five or ten minutes, but with a little button pushing and fingers working in and out, repeatedly and with increasing tempo, I turned my head to the side and buried my face in the nearest pillow to muffle my first orgasm of the night.

Brian sensed that it was time; I was wet enough and I knew the moment of losing my virginity was fast approaching. He reached over to grab a condom, unwrapped it and handed it to me, gesturing how to put it on correctly. I blushed and fumbled, but he took care of the rest, covering up my awkward moment with a kiss and nuzzle.

A brief look for acknowledgement and he guided himself past my nether lips, the first time I'd let anything other than fingers, tongue and toys in the past. And oh my, the feeling was amazing. After the first years of exploration, the times I got past the parental-controlled firewall to watch porn, the moment was finally here! It hurt of course, stung like a bee injury inside my pussy, but the pain finally ( and slowly) turned into pleasure and Brian continued to open up my wet, hot cunt. Finally--I wasn't a virgin any longer, and I loved it!

Not much went through my mind other than trying to hold onto every moment then and there, and obviously it didn't happen, since I only really remember watching that particular movie during it all. But I do remember Brian cumming hard, feeling him thrust erratically inside before pulling out and disposing of the blood-streaked, cum-filled latex condom. I did mess up his white duvet bed cover, and he had to stealth it across the house into the washing machine. I remember being beet red and trying to hide my face after his sister nearly barged in on my slight state of undress. I remember being pleasantly sore for days after, but trying to hide my elation and million watt smile until I could start exploring my sexuality again, in my next setting: the life-away-from home at college.

In those seven years since, I've met countless guys, some men but most boys. I've taken seventeen (or eighteen) as partners and thoroughly enjoyed sex with most of them. Some have provided my most loved kinks to this day, others have taught me valuable lessons in (and out) of the bed room. But I'll always have the fondest of memories of Brian, his back bed room, trying not to be the loud moaner that I am, and playing Donnie Darko as we fucked my virginity away in mid-August '06. To be frank, that movie still creeps me the fuck out when I'm not getting turned on by it.